


Adventures of Madeline and Louise

by wafflesmcpoptart



Category: Gilmore Girls
Genre: Cunnilingus, F/F, Hand Jobs, M/M, Multi, Sex, Threesome - F/F/F, Threesome - F/F/M, Vaginal Fingering
Language: English
Status: In-Progress
Published: 2020-04-25
Updated: 2020-04-25
Packaged: 2021-03-01 22:48:43
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 5
Words: 3,688
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/23814853
Author URL: https://archiveofourown.org/users/wafflesmcpoptart/pseuds/wafflesmcpoptart
Summary: Random sexcapades of Madeline and Louise.
Relationships: Madeline Lynn/Louise Grant, Madeline Lynn/Louise Grant/Max Medina, Madeline Lynn/Louise Grant/Paris Geller, Madeline Lynn/Louise Grant/Tristan Dugrey
Kudos: 2





	1. The Pool House

**Author's Note:**

> I own nothing.

After Rory ran out crying, Tristan found and broke into Madeline’s fathers alcohol stash. He gulped amber colored liquor straight from the bottle until he felt a head change. He started buzzing through the party, making his way out the back door, bottle in hand. He stopped at the pool, taking a swig, trying to decide if he should just fall in.

A flicker of light from the pool house caught his attention. He heard giggles as he got closer. Hazily through the window, he saw Madeline and Louise. Madeline’s back at least. Tristan’s vision was starting to double as Louise’s hand grabbed Madeline’s butt, pulling Madeline to her and kissing her. His breath caught and his dick sprang to life as Louise pulled Madeline’s shirt off.

Tristan found his liquid courage kicking in as he found his hand twisting the door knob open to walk in.

“Ladies, ladies, what do we have here?” Tristan grinned wider as he saw the boys that Madeline and Louise had been walking around the party with tried to cover their hard dicks.

“Tristan, hi,” Louise purred, pulling Madeline center closer to hers.

“Tristan?! Hi!” Madeline twisted, allowing Tristan to appreciate the side view of her breast.

“May I join this sub party? I bring booze,” Tristan offered up the bottle.

“You better replace that!” Madeline said, breaking away from Louise to retrieve the bottle from Tristans hand. He gazed upon her bare breasts as she took the bottle and threw it back, taking a large drink. He panted quietly as the liquor dripped down her chin, past her neck and stopped at the top of her perky breasts.

Louise took the opportunity to lean forward, tongue out. She started at Madeline’s nipple, circling her tongue around it before licking up her breast to the line of liquor. Madeline held the bottle to her side as Louise’s mouth met hers for a wet sloppy kiss.

Tristan noticed that the boys weren’t as worried about hiding their dicks anymore as they slowly slid their hands up and down their shafts.

“So do you all expect me to stay on the sidelines, or do I get to join in?” Tristan asked. Louise took the bottle from Madeline and took a large swig.

“Join the boys for now. You’ll have your chance.” Madeline grinned, sliding Tristans pants off and moving him to sit between the other two boys. 

Louise started to pull Madeline away by the hips, but not before Madeline reached out and took ahold of Tristans dick between her lips, and the other boys dicks in her hands. She swirled her tongue around the tip of Tristans dick like it was a sucker, popping it between her lips letting it go. She trailed her fingers one last time along the other boys shafts, before standing band turning to Louise.

Tristan and the other boys let out a frustrated grunt, taking their own dicks in hand again.

Madeline helped Louise shimmy out of her dress, leaving her in nothing but a black thong, before sliding her own skirt down her legs, bending in front of the boys to show them her bare ass.

Madeline and Louise stood together, their hard nipples grazing each other. Louise spoke as Madeline kissed on her neck and ran her fingers up and down Louise’s torso. “Before we go on, we need you boys to show you’re willing to be a part of this.”

Tristan had a feeling he knew what was happening by the smirk on their faces. He took another large swig from the dwindling bottle of liquor and passed it to the boys. 

“What do you want to see?” Tristan asked, placing each of his hands on each of the boys inner thighs, gently rubbing his thumbs in circles. Both of the guys jumped, but not away. They stared at him with large eyes. Tristan turned to the boys with dark hair, “Would you suck my dick while she sucks yours? Because I’d suck yours for her to suck mine,” Tristan propositioned.

“Now that is an idea.” Louise grins, turning to kiss Madeline. “That gets me hot, what about you?” Louise slid her hand between Madeline’s thighs, sliding her fingers through her slick folds. 

“I was already wet,” Madeline thrusted her hips forward, enveloping Louise’s slim fingers.

“So what do you want to see,” Louise asked Madeline casually as she slid two fingers in and out of Madeline’s bald wet slit.

“Mmm, I want to see one of them suck Tristans dick... but I also want to suck Tristans dick.” Madeline moaned, palming Louise’s breast, pinching her nipple.

“I’ve got plenty to go around.” Tristan spread his legs slightly. Both of his hands had massaged their way up both boys thighs, and he now had their dicks in his hands, gently caressing.

The dark haired boy leaned forward, taking Tristans dick in his hand, before taking him in his mouth.

“Well it seems we have a volunteer.” Louise grinned. “Go on, suck his dick.” Louise encouraged the boy, as well as Madeline. As Madeline got on her knees, Louise continued fingering her until she brought Madeline off, causing her to choke on cock.

Louise noticed their other boyfriend, his dick beginning to throb purple as Tristan pumped it, a little extra aggressive as he was probably about to pop himself from the blow job. Louise placed her lips around the tip of her boyfriends dicks, licking and sucking the head for a short time before his thick cum shot to the back of her throat. Tristans hand lightened up as she took one last suck. He lay his head back, spent.

Louise looked over to Madeline, noticing that her boyfriend no longer had Tristans cock in his mouth, as we was cumming down Madeline’s throat. 

“Me and you are still left to take care of,” Tristan’s voice was rough, as he looked Louise in the eyes. He pulled her on his lap, kissing her hard as his thumb rubbed circles on her clit. He sucked her lip as her breathing increased when Madeline reached from behind, entering 2 fingers in Louise’s pussy. Tristan sucked Louise’s nipple into his mouth as he and Madeline worked together to get Louise off. It wasn’t long before Louise was crying out, grinding harder onto both of their hands.

“Do you need a moment?” Tristan asked as Louise leaned back against Madeline.

“Oh no, you’ve helped make this night even hotter.” Louise gives Madeline a sloppy wet kiss before leaning down and licking the full length of Tristans dick. Madeline, wondering if this was their only chance, leaned forward to kiss Tristan. He kissed as good as she ever thought he would, his tongue with hers turning her on all over again. Madeline pulled away, kissed down his body so she was side by side with Louise.

Madeline places her tongue at the base of Tristans cock and followed Louise’s mouth as she pulled her mouth back to the tip. Madeline and Louise make out with the tip of Tristans cock between them. Madeline takes his shaft in her hand, lightly pulling and Louise continues to suck on the tip.

As Tristan cums down Louise’s throat, he pulls Madeline up for a hungry kiss.

“Well girls. That was fun. Seems your boys couldn’t keep up,” Tristan points out that both boys are asleep.

“I guess we’ll have to try this again without them sometime.” Louise shoots back. Tristan just smiles as he pulls on his clothes and leaves.


	2. Oh Romeo

”We have 30 minutes until Paris kills us for not being there on time,” Madeline says breathily and Louise kisses and licks at her neck, while Tristan’s middle and index fingers slide over Madeline’s clit and slick center.

“I can get you both off and still have time to stop for cigarettes,” Tristan brags, pulling Louise’s underwear down with his other hand. He sticks his face in the center of her clothed breasts as he reaches out his thumb to circle her clit.

“Challenge accepted,” Louise says, lifting her hips slightly toward him.

The girls lay side by side on their back in the back of Louise’s SUV. Tristan hovered over them, flexing his abs to hold himself up as he wasted no time inserting two fingers into both girls vaginal opening.

Madeline gasped, leaning forward to capture Tristans mouth with hers. Louise reaches her hand over to rub Madeline’s clit the way she knows she likes it. Madeline threw her head back as she ground her center hard against Louise and Tristans hands, grunting.

“She’s pretty easy if you know what she likes,” Louise grinned, leaning over to kiss Madeline while they both continue to ride Tristans fingers. 

“I’m, I’m good.” Madeline says rasping as her hips jerk away from their roaming hands. Madeline turns on her side towards Louise, “Your turn.”

Madeline catches Louise’s lips with hers, parting her lips to taste her tongue. Madeline tickled her fingers up Louise’s ribs, to take her nipple between her fingers and lightly twist while sucking Louise’s tongue into her mouth. Louise bucked her hips onto Tristans hand, enveloping his two thick fingers deep inside her pussy, thumb circling her clit, sending her over the edge after seconds. Tristan replaces his hand with his mouth and sucked the last bit of Louise’s juices until she pushed him away.

“I think you both know how to get eachother off pretty fast huh? We really might make it on time.” Tristan smirked as he licked his fingers, then wiped his mouth off.


	3. The Concert

**Summary for the Chapter:**

> When their dates didn’t work out...

When Paris cancelled the after school meeting for the paper, Madeline and Louise asked every boy they knew if they were available. Just when they thought they had found dates, they fell through. This left Madeline and Louise having a sleepover at Louise’s big empty mansion.

They lay on Louise’s bed in their pajamas watching movies, surrounded by snacks. Madeline threw back her head to spray some whipped cream in her mouth.

“Want some?” Madeline offers Louise. Louise’s eyes are fixed on the movie. Madeline looks to see two of the main characters making out.

“I’m horny, how could we not find dates?” Louise whined.

“You know I can help,” Madeline said, spraying some whipped cream on Louise’s neck before leaning forward and licking it off. Madeline was so skilled with her tongue, that it didn’t take Louise long to make up her mind. She knew what that tongue could do between her legs. 

“Get a toy that we can share,” Louise says breathily, leaning in to steal a kiss, pushing her tongue into Madeline’s mouth for a sloppy kiss. Madeline giddily ran to Louise’s drawer, grabbing the double sided dildo and vibrator. “I like the way you think.” Louise said, standing the meet Madeline halfway, but also so they could get undressed.

Before Louise could get her pants all the way off, Madeline was already putting the vibrator against her clit, giggling.

Louise let out a labored laugh at the instant sensation, as she felt her clit tighten. Louise pressed her bare breasts into Madeline’s, tilting her hips toward the vibrator. 

“Not so fast. Lay down on your back,” Madeline instructed. Louise did as told. She was a slave to Madeline when Madeline’s tongue on her was involved.

With Louise’s legs spread, Madeline leaned between them, gently caressing the vibrator against Louise’s dripping slit and hard clit. She sucked one of Louise’s nipples into her mouth, gently nibbling with her teeth before pressing the vibrator harder against Louise’s clit.

“Mmm, Mads... I need that mouth of yours, please.” Louise cooed, writhing beneath Madeline. 

“Don’t worry. You know I’ll take care of you,” Madeline says, sliding over Louise to give her a wet kiss. Louise brought her hand between them, flicking Madeline’s clit, before inserting two fingers into Madeline’s hot cunt.

“Ok, ok, ok,” Madeline moaned into Louise’s mouth. She sat up, straddling Louise’s stomach, riding Louise’s fingers. A circle of Louise’s thumb over Madeline’s clit had Madeline’s vaginal walls tightening and gushing around Louise’s fingers in no time.

“As fast as you make me cum, I definitely owe you.” Madeline said in a sensual voice, beginning to kiss her way down Louise’s body. She groaned as Louise licked her juices from her fingers one by one right as she got between Louise’s legs, licking her own thick wet stripe through her wet pussy lips.

Louise groaned at that first lick, but began writhing as Madeline skillfully dipped her tongue deep inside of her cunt, using her nose to rub against Louise’s clit. Madeline pulled her tongue back, licking up to Louise’s clit and gently suckling on it while inserting the tip of the vibrator into Louise’s tight lips.

“Oh god Madeline... ohhh.. ohh... get that dildo and fuck me please.” Louise groaned, her usually raspy voice even more sensual and sexy than normal.

Madeline inserted the double sided dildo into Louise’s dripping core before placing it within herself. They both groaned together, crossing their legs over each others to get as close and as deep as they could together. 

Slowly rocking back and forth against eachother, Louise pulls Madeline in for another wet kiss. “I’m so glad... that.. uh..huh.. that we can...oh god, Mads, faster. I’m about to cum.”

Madeline felt herself building, placing the vibrator between their rubbing clits. Madeline ground herself harder on to the dildo, grinding hard into Louise, sending them both over the edge, moaning aloud together. 

“Now what was that?” Madeline asked, giving one last pump before pulling the soaking toy from both of them.

“Just that I’m so glad we can help each other out in every way,” Louise grinned, one last sensual kiss before disappearing to the bathroom to shower. “You coming?”


	4. Sleepover

It was the night of high school graduation. Madeline, Louise, and Paris were all in Louise’s room after a party where everyone had been drinking to celebrate. The girls even managed to get Paris to partake in a few shots with them, leaving all three girls inebriated.

“So you’ve really never had an orgasm?” Madeline asks Paris, pointedly.

Paris blushes, “No, I mean, I’ve had sex with Jamie and it feels good. But I’ve never had that... explosion that I’ve heard you guys talk about.”

“Oh honey. What about when you masturbate?” Louise asks, beginning to take her party clothes off.

“I don’t really? Maybe my vagina is broken.” Paris sighs.

“Take your clothes off.” Louise instructed.

“Wait, what?” Paris looks between Madeline and Louise. “Take your clothes off. We are going to give you an orgasm, show you you aren’t broken.” Louise tells Paris, walking closer to her. “But I’m not into girls,” Paris hesitates, excited at the same time. “Everyone deserves to experience an orgasm Paris, now take off your clothes!” Madeline says, stripping her own clothes off. “Well...I guess to find out if I’m broken or not,” Paris looks down as she starts to take off her clothes, beginning with her shirt. Both Madeline and Louise were already naked before her, starting to touch each other , caressing each others breasts and sharing short kisses. “So what do I do?” Paris stood naked, awkwardly In the middle of Louises lavish bedroom. “Come here,” Madeline beckons to her to sit next to her on the bed. Paris joins her and Louise sits in front of them on the bed. “Do you want to watch us first, or ...?” Louise trailed off as she reached out and gently ran a finger down the side of Paris’s breast. Paris gulped, and squeaked out, “Me.” She was already dripping between her thighs from the little bit that Madeline and Louise had been kissing and touching each other. Madeline and Louise smiled at each other, looking at Paris like prey. 

Louise parted Paris’ legs, she circled her middle and index finger on Paris’s throbbing clit. Madeline pulled down the cups of Paris’s bra and attached her mouth to Paris’s nipple, lightly biting at it. “That feels nice,” Paris whimpers. Louise inserts two fingers inside of Paris’s wet slit, curling her fingers as she continues rubbing her clit. Within moments, Paris is writhing beneath them. “You like that, huh?” Louise’s husky voice asks as she lowers herself between Paris’s legs. Madeline is nipping and sucking at Paris’s nipples. Paris can only manage to get out a grunt, mixed with a scream at Louise’s mouth attached to her clit, licking her tongue through Paris’s dripping folds. Madeline’s hand joins in, gently rubbing circles on Paris’s clit. “I think... I’m definitely... I’m.. ahhh...” Paris’s vaginal walls clenched around Louise’s tongue, releasing her juices all over Louise’s face. Paris brings Madeline in for a wet sloppy kiss as Louise continues licking and sucking Paris’s clit and folds through her orgasm. “So how do I tell him how to do that?” Paris asks, laughing. “We could show him.” Madeline grins evilly.


	5. Mr. Medina

What was he doing here? These girls are his students. WERE. Were his students. They’re both 18, and graduation was a month ago. So this is totally legal.

But why does he feel so guilty as he sits back, rubbing his hard cock, watching Madeline and Louise make out and finger each other. He shouldn’t feel guilty though. They invited him here, they invited him to watch and join in.

He relaxed a little, leaning back a little as Louise kissed her way down Madeline’s bare chest. He sucked in a breath and felt his balls tighten as Louise took one of Madeline’s nipples in her mouth, while rolling the other between her fingers. Madeline threw her head back in ecstasy.

“I’m so ready for you,” Madeline moaned, writhing her body against Louise, hoping for some friction between her legs. Louise just grinned as she licked her way down Madeline’s flat stomach, all the way to her hot, dripping center.

Louise licked through Madeline’s wet folds, wanting to taste it all. She made a figure 8 around Madeline’s clit and slit, before sucking at her clit.

The girls had almost forgot Max was there until they heard him get up from where he had been sitting.

“I got lonely over there,” Max says, making his way toward the girls. Louise’s ass is in the air and very inviting. But Madeline reaches out to him.

Max makes the ultimate decision to live out his life long dream of a threesome with some of his previous students. He leans in for a soft kiss with Madeline, which she quickly turns wet and hot as Louise begins jutting her tongue as far into Madeline’s cunt as she can.

Madeline reaches out for Max’s cock, slowly pumping it.

“I always knew you’d be big.” Madeline grins, getting Louise’s attention.

“Oh, that is big,” Louise says, practically drooling. She chooses to pump her fingers into Madeline in order to move slightly to take Max’s dick from Madeline to suck on it.

Max can barely handle it. “Go back to eating out Madeline, get that ass back in the air.” He instructs.

Louise does as she’s told, excited for what’s to come.

Max aligns himself behind her, first leaning down and licking a strip from her clit to her asshole. A loud yet muffled moan came from Louise, which did not stay buried in Madeline’s cunt for much longer as Max pushed his large cock inside of her.

“Holy shit Max!” Louise moaned, pushing back with her hips, all while going back to sucking at Madeline’s clit, entering a few fingers to Madeline’s dripping hole.

“You’re as tight as I thought you’d be,” Max groans, pushing his cock in and out of Louise. He slowly rocked his hips back and forth, continuing to enjoy the view of Madeline’s naked body writhing beneath Louise, whose beautiful backside kept pushing harder against his hips, taking him as deep as she could. With that, he started pumping faster and harder. This caused Louise to start sucking on Madeline’s clit, continuing to fuck her with her fingers.

Louise was the first to cum, unable to handle Max’s large cock for long. She curled her fingers inside of Madeline’s cunt, with one last suckle to her clit as she groaned, cumming hard. Madeline not far behind, soaking Louise’s fingers and chin. 

“You girls are so sexy... but I’m not done yet,” Max said proudly, rubbing his swollen, gleaming wet cock. “Help me out?” Max stood, holding his cock near Madeline’s mouth. She licked her lips, before taking him whole, showing what that mouth could do. Louise crawled over, sitting behind Madeline so she could still touch her body, but also help lick Max’s fat cock.

“Let me taste him,” Louise licked along side of Madeline, continuing to finger her and make out at the tip of his dick.

“Madeline, why don’t you sit on my dick, and Louise come sit on my face?” Max propositioned. That was all it took for the girls to get in position. “This is like a dream,” Max said as Madeline slid onto his cock, while Louise’s cunt hovered over his face. He dove his face into her ass, licking deep into her asshole, holding her down the lick hard around the the front, jutting his tongue deep in her, while pumping his hips. 

With both girls writhing on Max’s appendages, they fell into eachother, caressing each other’s breasts, giving eachother the wettest tongue kisses, barely able to hold it together.

“Are you ready? I think I’m going to bust,” Max’s voice deeper than normal.

“Oh god yes Max. Fucking cum for us.” Madeline said, riding his dick as good as she can, while already coming undone herself. There was one last tongue thrust into Louise’s cunt before Max let go, letting his seed pump into Madeline. 

“I’ve wanted to do that since you first became our teacher,” Madeline admitted.

“I’ve wanted to do that since the first time I saw you making out in the hallway, whether with boys or each other.” Max confessed. 

“We only made out with each other in front of your room so that this would hopefully happen one day.”


End file.
